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6-(1,2-dimethyl-1H-imidazol-5-yl)hex-5-yn-1-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
127 mg
With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 80℃; for 3h;Inert atmosphere;
General procedure: To a solution of 2-disubstituted 1-methyl-1H-imidazole 1 (1 mmol) in DMF (5 mL), NBS(169 mg, 0,95 mmol) was added and the resulting reaction mixture was stirred in the dark at room temperature for 3h. Then, Pd(PPh3)2Cl2 (14 mg, 0.02 mmol, 2 mol%), CuI (8 mg, 0.04mmol, 4 mol%), an alkyne 3 (1,1 mmol) and piperidine (300 muL, 255 mg, 3 mmol) were added and the resulting reaction mixture was stirred at 80C (when trimethylsilylacetylene was employed as the alkyne, the reaction was carried out at 50C) for 3 h. The reaction mixture was diluted with EtOAc (100 mL), then saturated aqueous NH4Cl (100 mL) was added. The resulting mixture was stirred for 30 minutes and extracted with EtOAc (3x 25mL). The organic extracts were washed with water (3 x 25 mL) and brine (1 x 25 mL), driedover anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatogaraphy on silica gel. This procedure was employed to prepare compounds 4a-l. GLC analysis showed that all these compounds had chemical purity higherthan 98%.
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; at 25℃; for 3h;Inert atmosphere;
(a) In a 100 mL three-vial flask,5-hexyn-1-ol (1.5 mL, 13.6 mmol) was added in sequence,THF 30mL,Methyl N-(p-tosyl)carbamate I (3.27 g, 14.28 mmol),Replace nitrogen 3 times,PPh3 (3.93 g, 14.96 mmol) was added in that order.Diethyl azodicarboxylate (ie DEAD, 6.80 mL of 2.2M n-hexane, 14.96 mmol),Stir at 25°C for 3 hours and the reaction is complete.The reaction solution was concentrated to dryness, and the target product 1 was obtained by column chromatography (PE/EA=1/0 to 6/1, PE was petroleum ether, EA was ethyl acetate) (4.12 g, yield: 98percent).
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